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Synlett 2000; 2000(1): 104-106
DOI: 10.1055/s-2000-6459
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The Reductive Cleavage of Cyclic Aminol Ethers to N,N-Dialkylamino-derivatives: Modifications to the Eschweiler-Clarke Procedure

Philip C. Bulman Page* , Harry Heaney, Gerasimos A. Rassias, Serge Reignier, Edward P. Sampler, Salem Talib
  • *Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 3TU, UK; Fax + 44(15 09)22 39 25; E-mail: p.c.b.page@lboro.ac.uk or h.heaney@lboro.ac.uk
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Publication Date:
31 December 2000 (online)

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The reductive cleavage of cyclic aminol ethers to give N-alkylamino-derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.

aminol ethers - chiral heterocycles - chlorotrimethylsilane - reductive ring opening - sodium cyanoborohydride

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